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2,2-Dimethyloxirane can be cleaved by ac...

2,2-Dimethyloxirane can be cleaved by acid `(H^(o+))`. Write the mechanism.

Text Solution

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In the acidic medium, the oxygen atom of the oxirane ring gets protonated. The presence of positive charge on the oxygen atom weakens the C-O bond more on the side of `C_(2)` since the partial positive charge created on `C_(2)` will be stabilized by the +I-effect of the two `CH_(3)` groups in the transition state (T.S.). Consequently, the attac of the nucleophile, i.e., `H_(2)O` preferentially occurs on `C_(2)` yielding 2-methylpropan-1,2-diol.
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